#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/20/4102094.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4102094
loop_
_publ_author_name
'Nicholas E. Shepherd'
'Hirooki Tanabe'
'Yingjie Xu'
'Shigeki Matsunaga'
'Masakatsu Shibasaki'
_publ_section_title
;
 Direct Catalytic Asymmetric Vinylogous Mannich-Type and Michael Reactions
 of an α,β-Unsaturated γ-Butyrolactam under Dinuclear Nickel Catalysis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3666
_journal_page_last               3667
_journal_paper_doi               10.1021/ja1002636
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H19 Br N2 O5 '
_chemical_formula_sum            'C17 H19 Br N2 O5'
_chemical_formula_weight         411.25
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 109.5750(17)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   10.7145(3)
_cell_length_b                   7.1225(3)
_cell_length_c                   12.4937(3)
_cell_measurement_reflns_used    5260
_cell_measurement_temperature    103.1
_cell_measurement_theta_max      68.1
_cell_measurement_theta_min      3.8
_cell_volume                     898.34(5)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku & RAC 2007)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (Rigaku & RAC 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2002 (Burla, 2003)'
_diffrn_ambient_temperature      103.1
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.077
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9153
_diffrn_reflns_theta_full        68.21
_diffrn_reflns_theta_max         68.21
_exptl_absorpt_coefficient_mu    3.389
_exptl_absorpt_correction_T_max  0.661
_exptl_absorpt_correction_T_min  0.396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             420.00
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.80
_refine_diff_density_min         -0.48
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1355 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.039(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3134
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0790
_reflns_number_gt                2620
_reflns_number_total             3134
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja1002636_si_003.cif
_cod_data_source_block           '_091221'
_cod_original_cell_volume        898.35(5)
_cod_original_formula_sum        'C17 H19 Br N2 O5 '
_cod_database_code               4102094
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.06523(3) 0.33336(5) 0.21203(2) 0.02252(12) Uani 1 1 d . . .
O1 O 0.4277(2) 0.3595(5) 1.07217(18) 0.0274(7) Uani 1 1 d . . .
O2 O 0.6565(2) 0.3122(6) 1.01452(18) 0.0252(7) Uani 1 1 d . . .
O3 O 0.6082(2) 0.2848(3) 0.82344(19) 0.0192(7) Uani 1 1 d . . .
O4 O 0.3309(3) 0.9093(4) 0.6181(2) 0.0381(8) Uani 1 1 d . . .
O5 O 0.5091(3) 0.7486(4) 0.6434(3) 0.0405(9) Uani 1 1 d . . .
N1 N 0.4420(2) 0.3212(6) 0.8902(2) 0.0170(6) Uani 1 1 d . . .
N2 N 0.4035(3) 0.7772(5) 0.6589(3) 0.0229(8) Uani 1 1 d . . .
C1 C 0.3592(4) 0.4453(5) 0.6874(3) 0.0163(9) Uani 1 1 d . . .
H1 H 0.4459 0.4225 0.6759 0.020 Uiso 1 1 calc R . .
C2 C 0.3467(3) 0.2975(5) 0.7741(3) 0.0183(10) Uani 1 1 d . . .
H2 H 0.3592 0.1698 0.7459 0.022 Uiso 1 1 calc R . .
C3 C 0.2179(3) 0.3005(6) 0.7971(3) 0.0204(9) Uani 1 1 d . . .
H3 H 0.1336 0.2876 0.7399 0.024 Uiso 1 1 calc R . .
C4 C 0.2352(3) 0.3230(7) 0.9048(3) 0.0223(8) Uani 1 1 d . . .
H4 H 0.1658 0.3291 0.9360 0.027 Uiso 1 1 calc R . .
C5 C 0.3760(3) 0.3375(8) 0.9707(3) 0.0211(7) Uani 1 1 d . . .
C6 C 0.5799(3) 0.3046(6) 0.9200(3) 0.0198(10) Uani 1 1 d . . .
C7 C 0.7464(3) 0.2959(6) 0.8240(3) 0.0206(10) Uani 1 1 d . . .
C8 C 0.7262(4) 0.2864(6) 0.6968(3) 0.0296(13) Uani 1 1 d . . .
H8A H 0.8126 0.2861 0.6858 0.036 Uiso 1 1 calc R . .
H8B H 0.6750 0.3956 0.6584 0.036 Uiso 1 1 calc R . .
H8C H 0.6781 0.1712 0.6647 0.036 Uiso 1 1 calc R . .
C9 C 0.8243(4) 0.1301(7) 0.8875(4) 0.0293(12) Uani 1 1 d . . .
H9A H 0.9121 0.1289 0.8793 0.035 Uiso 1 1 calc R . .
H9B H 0.7773 0.0138 0.8563 0.035 Uiso 1 1 calc R . .
H9C H 0.8340 0.1401 0.9681 0.035 Uiso 1 1 calc R . .
C10 C 0.8071(4) 0.4837(6) 0.8743(4) 0.0287(12) Uani 1 1 d . . .
H10A H 0.7474 0.5860 0.8365 0.034 Uiso 1 1 calc R . .
H10B H 0.8926 0.5000 0.8628 0.034 Uiso 1 1 calc R . .
H10C H 0.8204 0.4857 0.9558 0.034 Uiso 1 1 calc R . .
C11 C 0.3640(4) 0.6439(5) 0.7340(3) 0.0185(8) Uani 1 1 d . . .
H11A H 0.2759 0.6790 0.7371 0.022 Uiso 1 1 calc R . .
H11B H 0.4287 0.6498 0.8120 0.022 Uiso 1 1 calc R . .
C12 C 0.2511(3) 0.4201(5) 0.5719(3) 0.0166(8) Uani 1 1 d . . .
C13 C 0.1246(4) 0.4908(6) 0.5463(3) 0.0210(9) Uani 1 1 d . . .
H13 H 0.1022 0.5584 0.6029 0.025 Uiso 1 1 calc R . .
C14 C 0.0293(4) 0.4659(5) 0.4403(3) 0.0194(9) Uani 1 1 d . . .
H14 H -0.0576 0.5147 0.4242 0.023 Uiso 1 1 calc R . .
C15 C 0.0639(3) 0.3682(6) 0.3584(3) 0.0178(9) Uani 1 1 d . . .
C16 C 0.1905(3) 0.2978(7) 0.3812(3) 0.0217(12) Uani 1 1 d . . .
H16 H 0.2138 0.2337 0.3239 0.026 Uiso 1 1 calc R . .
C17 C 0.2824(3) 0.3215(9) 0.4878(3) 0.0191(8) Uani 1 1 d . . .
H17 H 0.3686 0.2699 0.5045 0.023 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Br Br -0.676 1.280
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.031 0.018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.049 0.032
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O3 C7 121.0(3) . . ?
C6 N1 C5 123.4(3) . . ?
C6 N1 C2 124.8(3) . . ?
C5 N1 C2 111.2(2) . . ?
O4 N2 O5 123.7(4) . . ?
O4 N2 C11 118.6(3) . . ?
O5 N2 C11 117.7(3) . . ?
C11 C1 C12 112.8(3) . . ?
C11 C1 C2 111.4(3) . . ?
C12 C1 C2 111.4(3) . . ?
N1 C2 C3 100.8(3) . . ?
N1 C2 C1 114.6(3) . . ?
C3 C2 C1 115.1(3) . . ?
C4 C3 C2 112.2(3) . . ?
C3 C4 C5 110.6(3) . . ?
O1 C5 N1 126.3(3) . . ?
O1 C5 C4 128.5(3) . . ?
N1 C5 C4 105.2(3) . . ?
O2 C6 O3 127.2(3) . . ?
O2 C6 N1 125.1(3) . . ?
O3 C6 N1 107.7(3) . . ?
O3 C7 C9 109.7(3) . . ?
O3 C7 C10 109.7(3) . . ?
C9 C7 C10 112.6(3) . . ?
O3 C7 C8 101.5(3) . . ?
C9 C7 C8 111.8(3) . . ?
C10 C7 C8 111.0(3) . . ?
N2 C11 C1 109.3(3) . . ?
C13 C12 C17 118.3(3) . . ?
C13 C12 C1 123.4(3) . . ?
C17 C12 C1 118.2(3) . . ?
C12 C13 C14 121.8(4) . . ?
C13 C14 C15 118.4(3) . . ?
C16 C15 C14 121.1(3) . . ?
C16 C15 Br1 119.8(3) . . ?
C14 C15 Br1 119.1(3) . . ?
C17 C16 C15 119.2(4) . . ?
C16 C17 C12 121.1(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C15 1.904(3) . ?
O1 C5 1.212(3) . ?
O2 C6 1.192(4) . ?
O3 C6 1.347(4) . ?
O3 C7 1.480(4) . ?
O4 N2 1.219(4) . ?
O5 N2 1.227(4) . ?
N1 C6 1.402(4) . ?
N1 C5 1.414(3) . ?
N1 C2 1.478(4) . ?
N2 C11 1.492(4) . ?
C1 C11 1.523(5) . ?
C1 C12 1.528(5) . ?
C1 C2 1.548(5) . ?
C2 C3 1.501(5) . ?
C3 C4 1.306(4) . ?
C4 C5 1.460(4) . ?
C7 C9 1.509(5) . ?
C7 C10 1.528(6) . ?
C7 C8 1.533(4) . ?
C12 C13 1.379(5) . ?
C12 C17 1.394(5) . ?
C13 C14 1.386(5) . ?
C14 C15 1.387(5) . ?
C15 C16 1.384(5) . ?
C16 C17 1.376(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 29328643
